HU184960B - Process for preparing new derivatives of 3,7-diazabicyclo/3.3.1/ nonane - Google Patents
Process for preparing new derivatives of 3,7-diazabicyclo/3.3.1/ nonane Download PDFInfo
- Publication number
- HU184960B HU184960B HU812112A HU211281A HU184960B HU 184960 B HU184960 B HU 184960B HU 812112 A HU812112 A HU 812112A HU 211281 A HU211281 A HU 211281A HU 184960 B HU184960 B HU 184960B
- Authority
- HU
- Hungary
- Prior art keywords
- diazabicyclo
- formula
- dimethyl
- nonane
- preparation
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 5
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 34
- 238000002360 preparation method Methods 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 20
- -1 benzhydryl group Chemical group 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 12
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 150000004678 hydrides Chemical class 0.000 claims abstract description 7
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 239000002585 base Substances 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 17
- RLFKNWNVBRSKKR-UHFFFAOYSA-N 3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-ol Chemical compound C1N(C)CC2CN(C)CC1C2O RLFKNWNVBRSKKR-UHFFFAOYSA-N 0.000 claims description 15
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 239000002516 radical scavenger Substances 0.000 claims description 4
- YHBFIXQEFVCHEJ-UHFFFAOYSA-N (3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-yl) benzoate Chemical compound C1N(C)CC2CN(C)CC1C2OC(=O)C1=CC=CC=C1 YHBFIXQEFVCHEJ-UHFFFAOYSA-N 0.000 claims description 3
- IQVKNTDTLCRWJQ-UHFFFAOYSA-N 3-ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-ol Chemical compound C1N(C)CC2CN(CC)CC1C2O IQVKNTDTLCRWJQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- JYRSCMLJPXJTLI-UHFFFAOYSA-N 9h-xanthene-9-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)C3=CC=CC=C3OC2=C1 JYRSCMLJPXJTLI-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- RJCGZNCCVKIBHO-UHFFFAOYSA-N 1-chloro-4-fluorobenzene Chemical compound FC1=CC=C(Cl)C=C1 RJCGZNCCVKIBHO-UHFFFAOYSA-N 0.000 claims 1
- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 claims 1
- WWIVBKRVRYCKND-UHFFFAOYSA-N 9-(4-chlorophenoxy)-3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonane Chemical compound C1N(C)CC2CN(C)CC1C2OC1=CC=C(Cl)C=C1 WWIVBKRVRYCKND-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical class COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004953 trihalomethyl group Chemical group 0.000 abstract description 6
- 150000002367 halogens Chemical class 0.000 abstract description 5
- ZVEKSHODTOFEIR-UHFFFAOYSA-N 3,7-dimethyl-9-phenoxy-3,7-diazabicyclo[3.3.1]nonane Chemical compound C1N(C)CC2CN(C)CC1C2OC1=CC=CC=C1 ZVEKSHODTOFEIR-UHFFFAOYSA-N 0.000 abstract 1
- 230000002763 arrhythmic effect Effects 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 238000001953 recrystallisation Methods 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 231100000111 LD50 Toxicity 0.000 description 5
- 206010003119 arrhythmia Diseases 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- PTPQJKANBKHDPM-UHFFFAOYSA-N 3,7-diazabicyclo[3.3.1]nonane Chemical class C1NCC2CNCC1C2 PTPQJKANBKHDPM-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 4
- 230000003288 anthiarrhythmic effect Effects 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 229960004194 lidocaine Drugs 0.000 description 4
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000002061 vacuum sublimation Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000006793 arrhythmia Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- QCUBMMSSGQHMOO-UHFFFAOYSA-N (3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-yl) 4-ethoxy-3-methoxybenzoate Chemical compound C1=C(OC)C(OCC)=CC=C1C(=O)OC1C2CN(C)CC1CN(C)C2 QCUBMMSSGQHMOO-UHFFFAOYSA-N 0.000 description 2
- KSAZTFOYZXHOOR-WLHGVMLRSA-N (e)-but-2-enedioic acid;3,7-dimethyl-9-phenoxy-3,7-diazabicyclo[3.3.1]nonane Chemical compound OC(=O)\C=C\C(O)=O.C1N(C)CC2CN(C)CC1C2OC1=CC=CC=C1 KSAZTFOYZXHOOR-WLHGVMLRSA-N 0.000 description 2
- WVKZYADEOYSVLZ-WLHGVMLRSA-N (e)-but-2-enedioic acid;9-(4-chlorophenoxy)-3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonane Chemical compound OC(=O)\C=C\C(O)=O.C1N(C)CC2CN(C)CC1C2OC1=CC=C(Cl)C=C1 WVKZYADEOYSVLZ-WLHGVMLRSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 2
- 229940127291 Calcium channel antagonist Drugs 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000480 calcium channel blocker Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000005186 naphthyloxy group Chemical class C1(=CC=CC2=CC=CC=C12)O* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 229960001722 verapamil Drugs 0.000 description 2
- RAKQAQVZFKXKDV-UHFFFAOYSA-N (3,7-dibutyl-3,7-diazabicyclo[3.3.1]nonan-9-yl) 4-chlorobenzoate Chemical compound C1N(CCCC)CC2CN(CCCC)CC1C2OC(=O)C1=CC=C(Cl)C=C1 RAKQAQVZFKXKDV-UHFFFAOYSA-N 0.000 description 1
- PLASUPSQGJEBNB-UHFFFAOYSA-N (3,7-diethyl-3,7-diazabicyclo[3.3.1]nonan-9-yl) 4-chlorobenzoate;hydrate;dihydrochloride Chemical compound O.Cl.Cl.C1N(CC)CC2CN(CC)CC1C2OC(=O)C1=CC=C(Cl)C=C1 PLASUPSQGJEBNB-UHFFFAOYSA-N 0.000 description 1
- CQIQEPNNPOMBNL-UHFFFAOYSA-N (3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-yl) 2-chloro-4-nitrobenzoate Chemical compound C1N(C)CC2CN(C)CC1C2OC(=O)C1=CC=C([N+]([O-])=O)C=C1Cl CQIQEPNNPOMBNL-UHFFFAOYSA-N 0.000 description 1
- CPAYOJUPPZSCHK-UHFFFAOYSA-N (3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-yl) 2-chloropyridine-3-carboxylate Chemical compound C1N(C)CC2CN(C)CC1C2OC(=O)C1=CC=CN=C1Cl CPAYOJUPPZSCHK-UHFFFAOYSA-N 0.000 description 1
- PKOMPXWVBQRCSV-UHFFFAOYSA-N (3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-yl) 2-phenylacetate Chemical compound C1N(C)CC2CN(C)CC1C2OC(=O)CC1=CC=CC=C1 PKOMPXWVBQRCSV-UHFFFAOYSA-N 0.000 description 1
- HGQCAVAIYCYAJW-UHFFFAOYSA-N (3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-yl) 3-(4-chlorophenyl)prop-2-enoate Chemical compound C1N(C)CC2CN(C)CC1C2OC(=O)C=CC1=CC=C(Cl)C=C1 HGQCAVAIYCYAJW-UHFFFAOYSA-N 0.000 description 1
- RRWNZNDJLMGFKH-UHFFFAOYSA-N (3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-yl) 3-(4-methoxyphenyl)prop-2-enoate Chemical compound C1=CC(OC)=CC=C1C=CC(=O)OC1C2CN(C)CC1CN(C)C2 RRWNZNDJLMGFKH-UHFFFAOYSA-N 0.000 description 1
- CXHHBYMWTBQOCA-UHFFFAOYSA-N (3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-yl) 4-chlorobenzoate Chemical compound C1N(C)CC2CN(C)CC1C2OC(=O)C1=CC=C(Cl)C=C1 CXHHBYMWTBQOCA-UHFFFAOYSA-N 0.000 description 1
- SQZLCHWKFNGZMV-UHFFFAOYSA-N (3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-yl) 4-ethylbenzoate Chemical compound C1=CC(CC)=CC=C1C(=O)OC1C2CN(C)CC1CN(C)C2 SQZLCHWKFNGZMV-UHFFFAOYSA-N 0.000 description 1
- SEISYXJHDPGALV-UHFFFAOYSA-N (3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-yl) 4-methylbenzoate Chemical compound C1N(C)CC2CN(C)CC1C2OC(=O)C1=CC=C(C)C=C1 SEISYXJHDPGALV-UHFFFAOYSA-N 0.000 description 1
- VDELVVCPNVJPBQ-UHFFFAOYSA-N (3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-yl) 4-nitrobenzoate Chemical compound C1N(C)CC2CN(C)CC1C2OC(=O)C1=CC=C([N+]([O-])=O)C=C1 VDELVVCPNVJPBQ-UHFFFAOYSA-N 0.000 description 1
- FYJLIJJCGDYGGM-UHFFFAOYSA-N (3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-yl) pyridine-3-carboxylate Chemical compound C1N(C)CC2CN(C)CC1C2OC(=O)C1=CC=CN=C1 FYJLIJJCGDYGGM-UHFFFAOYSA-N 0.000 description 1
- NKKKNIDNHXMDAV-UHFFFAOYSA-N 1,2-diazabicyclo[3.3.1]nonan-9-ol Chemical compound N12NCCC(CCC1)C2O NKKKNIDNHXMDAV-UHFFFAOYSA-N 0.000 description 1
- KTSZYXNHBVWNNV-UHFFFAOYSA-N 1,2-diazabicyclo[3.3.1]nonane Chemical compound C1CNN2CCCC1C2 KTSZYXNHBVWNNV-UHFFFAOYSA-N 0.000 description 1
- BDVKAMAALQXGLM-UHFFFAOYSA-N 1-ethylpiperidin-4-one Chemical compound CCN1CCC(=O)CC1 BDVKAMAALQXGLM-UHFFFAOYSA-N 0.000 description 1
- GBOWGKOVMBDPJF-UHFFFAOYSA-N 1-fluoro-3-(trifluoromethyl)benzene Chemical compound FC1=CC=CC(C(F)(F)F)=C1 GBOWGKOVMBDPJF-UHFFFAOYSA-N 0.000 description 1
- HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 description 1
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 description 1
- ULGWJLDMLZBZLH-UHFFFAOYSA-N 3,7-dibutyl-3,7-diazabicyclo[3.3.1]nonan-9-ol Chemical compound C1N(CCCC)CC2CN(CCCC)CC1C2O ULGWJLDMLZBZLH-UHFFFAOYSA-N 0.000 description 1
- JDZITGDSCMKQPR-UHFFFAOYSA-N 3,7-dibutyl-3,7-diazabicyclo[3.3.1]nonan-9-one Chemical compound C1N(CCCC)CC2CN(CCCC)CC1C2=O JDZITGDSCMKQPR-UHFFFAOYSA-N 0.000 description 1
- KLCVNFNVNKHMQJ-UHFFFAOYSA-N 3,7-diethyl-1,2-diazabicyclo[3.3.1]nonan-9-ol Chemical compound C(C)C1NN2CC(CC(C1)C2O)CC KLCVNFNVNKHMQJ-UHFFFAOYSA-N 0.000 description 1
- RTBZSELCZDDKIJ-UHFFFAOYSA-N 3,7-diethyl-3,7-diazabicyclo[3.3.1]nonan-9-ol Chemical compound C1N(CC)CC2CN(CC)CC1C2O RTBZSELCZDDKIJ-UHFFFAOYSA-N 0.000 description 1
- ATBBDQLQVYDBED-UHFFFAOYSA-N 3,7-diethyl-3,7-diazabicyclo[3.3.1]nonan-9-one Chemical compound C1N(CC)CC2CN(CC)CC1C2=O ATBBDQLQVYDBED-UHFFFAOYSA-N 0.000 description 1
- CWRKZBVVWVRVMS-UHFFFAOYSA-N 3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-one Chemical compound C1N(C)CC2CN(C)CC1C2=O CWRKZBVVWVRVMS-UHFFFAOYSA-N 0.000 description 1
- DXBFAQDHEPLJJC-UHFFFAOYSA-N 3,7-dimethyl-9-[3-(trifluoromethyl)phenoxy]-3,7-diazabicyclo[3.3.1]nonane;dihydrochloride Chemical compound Cl.Cl.C1N(C)CC2CN(C)CC1C2OC1=CC=CC(C(F)(F)F)=C1 DXBFAQDHEPLJJC-UHFFFAOYSA-N 0.000 description 1
- NFFPFTGFVSWSTH-UHFFFAOYSA-N 3-(3,4,5-trimethoxyphenyl)prop-2-enoyl chloride Chemical compound COC1=CC(C=CC(Cl)=O)=CC(OC)=C1OC NFFPFTGFVSWSTH-UHFFFAOYSA-N 0.000 description 1
- ZFOVCSTVYYYRSU-UHFFFAOYSA-N 3-(4-chlorophenyl)prop-2-enoyl chloride Chemical compound ClC(=O)C=CC1=CC=C(Cl)C=C1 ZFOVCSTVYYYRSU-UHFFFAOYSA-N 0.000 description 1
- CGOJOQBYEAVATL-UHFFFAOYSA-N 3-(4-methoxyphenyl)prop-2-enoyl chloride Chemical compound COC1=CC=C(C=CC(Cl)=O)C=C1 CGOJOQBYEAVATL-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- XXFKOBGFMUIWDH-UHFFFAOYSA-N 4-chloro-2-methylbenzoic acid Chemical compound CC1=CC(Cl)=CC=C1C(O)=O XXFKOBGFMUIWDH-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical class [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 1
- UFXLGVBYUIDHFW-WLHGVMLRSA-N 9-benzhydryloxy-3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonane;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.C1N(C)CC2CN(C)CC1C2OC(C=1C=CC=CC=1)C1=CC=CC=C1 UFXLGVBYUIDHFW-WLHGVMLRSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 208000033988 Device pacing issue Diseases 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- DULCUDSUACXJJC-UHFFFAOYSA-N Ethyl phenylacetate Chemical compound CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001501 aryl fluorides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- OQROAIRCEOBYJA-UHFFFAOYSA-N bromodiphenylmethane Chemical compound C=1C=CC=CC=1C(Br)C1=CC=CC=C1 OQROAIRCEOBYJA-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002964 excitative effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- RHMQNXNXUZLEIY-UHFFFAOYSA-N methanol;2-propan-2-yloxypropane Chemical compound OC.CC(C)OC(C)C RHMQNXNXUZLEIY-UHFFFAOYSA-N 0.000 description 1
- LXNFVVDCCWUUKC-UHFFFAOYSA-N methyl 4-chlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1 LXNFVVDCCWUUKC-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 230000036279 refractory period Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (41)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU812112A HU184960B (en) | 1981-07-20 | 1981-07-20 | Process for preparing new derivatives of 3,7-diazabicyclo/3.3.1/ nonane |
| ZA824809A ZA824809B (en) | 1981-07-20 | 1982-07-06 | New bicyclic compounds and a process for the preparation thereof |
| IL66277A IL66277A (en) | 1981-07-20 | 1982-07-08 | 3,7-dialkyl-3,7-diazabicyclo(3.3.1)nonan-9-ol derivatives,a process for the preparation thereof and pharmaceutical compositions containing them |
| CA000407149A CA1254208A (en) | 1981-07-20 | 1982-07-13 | 3,7-diazabicyclo¬3.3.1|nonanes and preparation thereof |
| AT0272382A AT379809B (de) | 1981-07-20 | 1982-07-13 | Verfahren zur herstellung von neuen 3,7-diazabicyclo/3,3,1/ nonanderivaten, deren stereoisomeren und physiologisch vertraeglichen saeureadditionssalzen |
| FI822526A FI71320C (fi) | 1981-07-20 | 1982-07-15 | Foerfarande foer framstaellning av nya antiarytmiska etrar ochestrar av 3,7-diazabicyklo/3.3.1/nonan-9-oler |
| CH4315/82A CH653032A5 (de) | 1981-07-20 | 1982-07-15 | Bicyclische verbindungen, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel. |
| GR68779A GR76874B (en, 2012) | 1981-07-20 | 1982-07-15 | |
| US06/398,801 US4451473A (en) | 1981-07-20 | 1982-07-16 | 3,7-Diazabicyclo [3.3.1] nonanes having anti-arrhythmic activity |
| PT75265A PT75265B (en) | 1981-07-20 | 1982-07-16 | Process for the preparation of diazabicyclicononanes substituted and pharmaceutical composition containing them |
| DD82241725A DD202575A5 (de) | 1981-07-20 | 1982-07-16 | Verfahren zur herstellung neuer bicyclischer verbindungen |
| DK319982A DK160875C (da) | 1981-07-20 | 1982-07-16 | Analogifremgangsmaade til fremstilling af 3,7-diazabicyklooe3.3.1aa-nonanforbindelser eller farmaceutisk acceptable syreadditionssalte deraf |
| GB08220818A GB2102801B (en) | 1981-07-20 | 1982-07-19 | New bicyclic compounds of the general formula (i) |
| IT22448/82A IT1190920B (it) | 1981-07-20 | 1982-07-19 | Composti biciclici e procedimento per la loro preparazione |
| NL8202908A NL8202908A (nl) | 1981-07-20 | 1982-07-19 | Nieuwe bicyclische verbindingen en werkwijze voor het bereiden daarvan. |
| SU823465423A SU1222197A3 (ru) | 1981-07-20 | 1982-07-19 | Способ получени бициклических соединений или стереоизомеров этих соединений или их фармацевтически приемлемых солей с кислотами |
| FR8212572A FR2510575B1 (fr) | 1981-07-20 | 1982-07-19 | Nouveaux composes bicycliques, leur procede de preparation et composition pharmaceutique les renfermant |
| MX193658A MX159288A (es) | 1981-07-20 | 1982-07-19 | Procedimiento para la preparacion de derivados de 3,7-diazabisiclo(3,3-1)nonano |
| JP57125600A JPS5849383A (ja) | 1981-07-20 | 1982-07-19 | ３，７―ジアザビシクロ〔３，３，１〕ノナン誘導体、その製法および抗不整脈剤組成物 |
| YU157182A YU45867B (sh) | 1981-07-20 | 1982-07-19 | Postupak za dobijanje derivata 3,7-diazabiciklo (3,3,1) nonana |
| AR290016A AR230447A1 (es) | 1981-07-20 | 1982-07-19 | Procedimiento para la preparacion de nuevos derivados sustituidos de 3,7-diazabiciclo-3,3,1-nonano,y procedimiento para la preparacion de las sustancias iniciales para dicho procedimiento |
| PH27586A PH18502A (en) | 1981-07-20 | 1982-07-19 | New bicyclic compounds and a process for the preparation thereof |
| ES514126A ES8401972A1 (es) | 1981-07-20 | 1982-07-19 | "un procedimiento para la preparacion de un nuevo compuesto biciclico". |
| CS825520A CS235302B2 (en) | 1981-07-20 | 1982-07-19 | Method of bicyclic compounds production |
| AU86176/82A AU552770B2 (en) | 1981-07-20 | 1982-07-19 | Diazabicyclo nonawe |
| SI8211571A SI8211571A8 (sl) | 1981-07-20 | 1982-07-19 | Postopek za pridobivanje derivatov 3,7-diazabiciklo (3,3,1) nonanov |
| DE3226921A DE3226921C2 (de) | 1981-07-20 | 1982-07-19 | Neue 3,7-Diazabicyclo[3.3.1]nonan Verbindungen und Verfahren zu ihrer Herstellung |
| SE8204393A SE450704B (sv) | 1981-07-20 | 1982-07-19 | 3,7-diazabicyklo /3,3,1/ nonaner, forfarande for framstellning och farmaceutisk beredning derav |
| NO822485A NO157421C (no) | 1981-07-20 | 1982-07-19 | Analogifremgangsmaate ved fremstilling av terapeutisk aktive 3,7-diazabicyclo-(3.3.1)-nonan-derivater. |
| BE0/208636A BE893891A (fr) | 1981-07-20 | 1982-07-20 | Nouveaux composes bicycliques, leur procede de preparation et composition pharmaceutique les renfermant |
| PL1982244329A PL135814B1 (en) | 1981-07-20 | 1982-07-20 | Process for preparing novel bocyclic compounds |
| PL1982237566A PL135878B1 (en) | 1981-07-20 | 1982-07-20 | Process for preparing novel bicyclic compounds |
| IN832/CAL/82A IN155994B (en, 2012) | 1981-07-20 | 1982-07-20 | |
| CS831747A CS235316B2 (cs) | 1981-07-20 | 1983-03-14 | Způsob výroby bicyklických sloučenin |
| ES520567A ES520567A0 (es) | 1981-07-20 | 1983-03-14 | Un procedimiento para la preparacion de un nuevo compuesto biciclico. |
| SU833646755A SU1272990A3 (ru) | 1981-07-20 | 1983-09-22 | Способ получени производных диазабицикло /3,3,1/ нонана или их солей |
| IN369/MAS/84A IN160649B (en, 2012) | 1981-07-20 | 1984-05-21 | |
| AT334984A AT379810B (de) | 1981-07-20 | 1984-10-19 | Verfahren zur herstellung von neuen 3,7-diazabicyclo (3,3,1) nonanderivaten, deren stereoisomeren und physiologisch vertraeglichen saeureadditionssalzen |
| HR920785A HRP920785A2 (en) | 1981-07-20 | 1992-10-01 | New bicyclic compounds and a process for the preparation thereof |
| LV930040A LV5258A3 (lv) | 1981-07-20 | 1993-01-18 | Diazabiciklo(3,3,1)nonana atvasinajumu vai to saju iegusanas panemiens |
| LV930048A LV5259A3 (lv) | 1981-07-20 | 1993-01-18 | Biciklisko savienojumu vai so savienojumu stereoizomeru vai to farmaceitiski pienemamu saju ar skabem iegusanas panemiens |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU812112A HU184960B (en) | 1981-07-20 | 1981-07-20 | Process for preparing new derivatives of 3,7-diazabicyclo/3.3.1/ nonane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU184960B true HU184960B (en) | 1984-11-28 |
Family
ID=10957812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU812112A HU184960B (en) | 1981-07-20 | 1981-07-20 | Process for preparing new derivatives of 3,7-diazabicyclo/3.3.1/ nonane |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4451473A (en, 2012) |
| JP (1) | JPS5849383A (en, 2012) |
| AR (1) | AR230447A1 (en, 2012) |
| AT (1) | AT379809B (en, 2012) |
| AU (1) | AU552770B2 (en, 2012) |
| BE (1) | BE893891A (en, 2012) |
| CA (1) | CA1254208A (en, 2012) |
| CH (1) | CH653032A5 (en, 2012) |
| CS (1) | CS235302B2 (en, 2012) |
| DD (1) | DD202575A5 (en, 2012) |
| DE (1) | DE3226921C2 (en, 2012) |
| DK (1) | DK160875C (en, 2012) |
| ES (2) | ES8401972A1 (en, 2012) |
| FI (1) | FI71320C (en, 2012) |
| FR (1) | FR2510575B1 (en, 2012) |
| GB (1) | GB2102801B (en, 2012) |
| GR (1) | GR76874B (en, 2012) |
| HU (1) | HU184960B (en, 2012) |
| IL (1) | IL66277A (en, 2012) |
| IN (1) | IN155994B (en, 2012) |
| IT (1) | IT1190920B (en, 2012) |
| MX (1) | MX159288A (en, 2012) |
| NL (1) | NL8202908A (en, 2012) |
| NO (1) | NO157421C (en, 2012) |
| PH (1) | PH18502A (en, 2012) |
| PL (2) | PL135814B1 (en, 2012) |
| PT (1) | PT75265B (en, 2012) |
| SE (1) | SE450704B (en, 2012) |
| SU (2) | SU1222197A3 (en, 2012) |
| YU (1) | YU45867B (en, 2012) |
| ZA (1) | ZA824809B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5036153A (en) * | 1989-05-11 | 1991-07-30 | Braish Tamim F | Preparation of 2,5-diazabicyclo[2.2.1]heptanes and intermediates |
| HUT74682A (en) * | 1993-12-29 | 1997-01-28 | Pfizer | Diazabicyclic neurokinin antagonists and pharmaceutical compositions containing them |
| GB9726630D0 (en) * | 1997-12-18 | 1998-02-18 | Glaxo Group Ltd | Kv2.1 Antagonists |
| MXPA02005884A (es) * | 1999-12-14 | 2002-10-23 | Neurosearch As | Heteroaril-diazabicicloalcanos novedosos. |
| AU2005228289B2 (en) | 2004-03-31 | 2008-01-10 | Nippon Soda Co., Ltd. | Cyclic amine compound and pest control agent |
| WO2007040280A1 (ja) | 2005-10-06 | 2007-04-12 | Nippon Soda Co., Ltd. | 環状アミン化合物および有害生物防除剤 |
| UA86328C2 (uk) * | 2005-10-06 | 2009-04-10 | Ниппон Сода Ко., Лтд. | Циклічні амінові сполуки, засіб для боротьби зі шкідниками |
| RU2503663C2 (ru) * | 2007-04-27 | 2014-01-10 | Актелион Фармасьютиклз Лтд | Мостиковые шестичленные циклические соединения |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3078272A (en) * | 1963-02-19 | N-aza-bicyclo-alkylene-imino | ||
| DE2428792A1 (de) * | 1974-06-14 | 1976-01-02 | Knoll Ag | Neue antiarrhythmika |
| DE2726571A1 (de) * | 1977-06-13 | 1978-12-21 | Basf Ag | Neue bispidinderivate, verfahren zu deren herstellung und arzneimittel, welche diese enthalten |
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1981
- 1981-07-20 HU HU812112A patent/HU184960B/hu not_active IP Right Cessation
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1982
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- 1982-07-16 DK DK319982A patent/DK160875C/da active
- 1982-07-16 DD DD82241725A patent/DD202575A5/de not_active IP Right Cessation
- 1982-07-16 US US06/398,801 patent/US4451473A/en not_active Expired - Lifetime
- 1982-07-19 GB GB08220818A patent/GB2102801B/en not_active Expired
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- 1982-07-19 ES ES514126A patent/ES8401972A1/es not_active Expired
- 1982-07-19 CS CS825520A patent/CS235302B2/cs unknown
- 1982-07-19 FR FR8212572A patent/FR2510575B1/fr not_active Expired
- 1982-07-19 IT IT22448/82A patent/IT1190920B/it active
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- 1982-07-19 PH PH27586A patent/PH18502A/en unknown
- 1982-07-19 AU AU86176/82A patent/AU552770B2/en not_active Ceased
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- 1982-07-19 JP JP57125600A patent/JPS5849383A/ja active Granted
- 1982-07-19 NL NL8202908A patent/NL8202908A/nl not_active Application Discontinuation
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1983
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |